AR044070A1 - DERIVATIVES OF 2 -ACILAMINO -4- FENILTIAZOL, ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS - Google Patents

DERIVATIVES OF 2 -ACILAMINO -4- FENILTIAZOL, ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS

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Publication number
AR044070A1
AR044070A1 ARP040101382A ARP040101382A AR044070A1 AR 044070 A1 AR044070 A1 AR 044070A1 AR P040101382 A ARP040101382 A AR P040101382A AR P040101382 A ARP040101382 A AR P040101382A AR 044070 A1 AR044070 A1 AR 044070A1
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AR
Argentina
Prior art keywords
alk
group
alkyl
conr4
formula
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ARP040101382A
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Spanish (es)
Inventor
Daniel Floutard
Pierre Fraisse
Samir Jegham
Bernard Labeeuw
Pierre Carayon
Pierre Casellas
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Sanofi Aventis
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Publication date
Application filed by Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR044070A1 publication Critical patent/AR044070A1/en

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Abstract

Procedimiento de preparación intermediarios, composiciones farmacéuticas y usos del presente. Reivindicación 1: Compuestos que responden a la fórmula (1), en la cual: R1 representa un átomo de hidrógeno o de halógeno, un grupo alquilo (C1-4), trifluoroetilo, hidroxilo, alcoxi (C1-4), trifluorometoxi, trifluoroetoxi, cicloalquiloxi (C3-8), aliloxi, ciclopropilmetoxi, alquiltio (C1-4); R2 representa un átomo de hidrógeno o de halógeno, un grupo alquilo (C1-8), trifluoroetilo, perfluoroalquilo (C1-4), cicloalquilo (C3-10), fenilo, alcoxi (C1-8), trifluorometoxi, trifluoroetoxi, aliloxi, cicloalquilmetoxi (C3-8), cicloalquiloxi (C3-8), cicloalquilmetilo (C3-8); R3 representa un grupo elegido entre: a) -O-alk(C2-4)-A; -O- alk(C1-4)-B; -O-E; b) -alk(C1-4)-A; c) -B; d) -alk(C1-4)-NR4-alk(C2-3)-A; -alk(C1-4)-NR4-alk(C1-3)-B; e) -CONR4-alk(C2-4)-A; -CONR4-alk(C1-4)-B; -CONR4-E; f) -CO-D-alk(C1-2)-A; -CO-G-A; o un resto seleccionado del grupo de fórmulas (2); R4 representa un átomo de hidrógeno o un grupo alquilo (C1-4); A representa un grupo NR5R6; B representa un grupo de fórmula (3); D representa un grupo de fórmula (4); E representa un grupo de fórmula (5); G representa un grupo de fórmula (6); R5 y R6 representan cada uno, independientemente entre sí, un átomo de hidrógeno, un grupo alquilo (C1-6), alilo, alk (C2-4), -O-alquilo (C1-4), alk(2-4)-OH, alk(C1-3)-CON(R4)2, alk(C2-3)-NHCO-alquilo (C1-4), cicloalquilo (C3-7), cicloalquilmetilo (C3-7), - CO-alquilo (C1-4), pirrolidinilo eventualmente sustituido por un grupo -CO-alquilo (C1-4), bencilo, tetrahidropiranilo, tetrahidropiranilmetilo, dimetiltetrahidropiranilo, tetrahidrofurilo, tetrahidrofurilmetilo; o R5 y R6 junto con el átomo de nitrógeno al cual están unidos constituyen un radical heterocíclico elegido entre: aziridinilo, azetidinilo, pirrolidinilo, piperidinilo, perhidroazepinilo, morfolinilo, piperazinilo, tropanilo, quinuclidinilo, 2-azabiciclo[2,2,1]heptanilo, 2- azabiciclo[2,2,2]octanilo, dichos radicales heterocíclicos están no sustituidos o sustituidos por un grupo fenilo, halogenofenilo, trifluorometilfenilo, trifluorometilo, hidroxi, metoxi, hidroximetilo, metoximetilo, formamido, trifluoroacetilamino, un grupo -NR4R7, tetrahidropiran-4-ilamino, -CON(R4)2, -CONR4R'4, -CH2CON(R4)2, alquilo(C1-4)-CONR4-, cicloalquilo(C3-8)-CONR4-, alquilo(C1-4)-OCONR4-, cicloalquilo(C3-8)-OCONR4-, (alquilo(C1-4)-OCO-)2N-, alquilo(C1-4)-COO-; o sustituidos por uno o varios grupos metilo; R'4 representa un grupo (CH2)s unido al átomo de carbono portador de -CONR4R'4; R7 representa un átomo de hidrógeno, un alquilo (C1-4), un grupo -SO2CH3 o R4 y R7 junto con el átomo de nitrógeno al cual están unidos constituyen un radical pirrolidinilo o piperidinilo; p representa 1, 2, 3, 4 ó 5; q representa 0, 1 ó 2; r representa 1 ó 2; s representa 2 ó 3; p + q es inferior o igual a 5; p + r es inferior o igual a 5; alk representa un alquileno; a condición de que R1 y R2 no sean simultáneamente un átomo de hidrógeno, en estado de base o de sal de adición con un ácido, así como también en estado de hidrato o de solvato.Intermediate preparation procedure, pharmaceutical compositions and uses herein. Claim 1: Compounds that respond to formula (1), in which: R 1 represents a hydrogen or halogen atom, a (C 1-4) alkyl, trifluoroethyl, hydroxyl, (C 1-4) alkoxy, trifluoromethoxy, trifluoroethoxy group , C 3-8 cycloalkyloxy, allyloxy, cyclopropylmethoxy, C 1-4 alkylthio; R2 represents a hydrogen or halogen atom, a (C1-8) alkyl, trifluoroethyl, perfluoroalkyl (C1-4), cycloalkyl (C3-10), phenyl, (C1-8) alkoxy, trifluoromethoxy, trifluoroethoxy, allyloxy group, cycloalkylmethoxy (C3-8), cycloalkyloxy (C3-8), cycloalkylmethyl (C3-8); R3 represents a group chosen from: a) -O-alk (C2-4) -A; -O- alk (C1-4) -B; -O-E; b) -alk (C1-4) -A; c) -B; d) -alk (C1-4) -NR4-alk (C2-3) -A; -alk (C1-4) -NR4-alk (C1-3) -B; e) -CONR4-alk (C2-4) -A; -CONR4-alk (C1-4) -B; -CONR4-E; f) -CO-D-alk (C1-2) -A; -CO-G-A; or a remainder selected from the group of formulas (2); R4 represents a hydrogen atom or a (C1-4) alkyl group; A represents an NR5R6 group; B represents a group of formula (3); D represents a group of formula (4); E represents a group of formula (5); G represents a group of formula (6); R5 and R6 each represent, independently from each other, a hydrogen atom, a (C1-6) alkyl, allyl, alk (C2-4), -O-(C1-4) alkyl, alk (2-4) group -OH, alk (C1-3) -CON (R4) 2, alk (C2-3) -NHCO-alkyl (C1-4), cycloalkyl (C3-7), cycloalkylmethyl (C3-7), - CO-alkyl (C1-4), pyrrolidinyl optionally substituted by a group -CO-(C1-4) alkyl, benzyl, tetrahydropyranyl, tetrahydropyranylmethyl, dimethyltetrahydropyranyl, tetrahydrofuryl, tetrahydrofurylmethyl; or R5 and R6 together with the nitrogen atom to which they are attached constitute a heterocyclic radical chosen from: aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, perhydroazepinyl, morpholinyl, piperazinyl, tropanyl, quinuclidinyl, 2-azabicyclo [2,2,1] heptanyl , 2- azabicyclo [2,2,2] octanyl, said heterocyclic radicals are unsubstituted or substituted by a phenyl, halogenophenyl, trifluoromethylphenyl, trifluoromethyl, hydroxy, methoxy, hydroxymethyl, methoxymethyl, formamide, trifluoroacetylamino, a -NR4R7, tetrahydropyran group -4-ylamino, -CON (R4) 2, -CONR4R'4, -CH2CON (R4) 2, (C1-4) alkyl -CONR4-, cycloalkyl (C3-8) -CONR4-, (C1-4) alkyl -OCONR4-, (C3-8) cycloalkyl -OCONR4-, ((C1-4) alkyl -OCO-) 2N-, (C1-4) alkyl -COO-; or substituted by one or several methyl groups; R'4 represents a group (CH2) s attached to the carbon atom bearing -CONR4R'4; R7 represents a hydrogen atom, a (C1-4) alkyl, a group -SO2CH3 or R4 and R7 together with the nitrogen atom to which they are attached constitute a pyrrolidinyl or piperidinyl radical; p represents 1, 2, 3, 4 or 5; q represents 0, 1 or 2; r represents 1 or 2; s represents 2 or 3; p + q is less than or equal to 5; p + r is less than or equal to 5; alk represents an alkylene; provided that R1 and R2 are not simultaneously a hydrogen atom, in the base or addition salt state with an acid, as well as in the hydrate or solvate state.

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